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The most awkward Awkward moments from The Graduates and Holding On and Letting Go

The whole gang graduates.

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MTV

MTV’s Awkward lives up to its name — and each week, EW will chronicle the comedy-drama’s most uncomfortable moments. This time, we’re looking at the season 5 midseason finale, also known as “The Graduates” and “Holding On and Letting Go,” where the whole gang graduates. Here are the 10 most awkward moments from these episodes of Awkward in chronological order.

1. Good news: Jenna and Matty are back together and having a grand old time having sex (so much sex) and innocently spending their mornings cuddling in bed. Bad news: Lacey barges into Jenna’s room one morning and sees Matty, who was sneakily spending the night, in her daughter’s bed. Worse news: Matty has a full-on boner. At least Lacey’s cool about it? (Oh, relax, Jenna, we know you’re sexually active,” she explains.)

2. Sadie was banned from walking at graduation when a chaperone caught her with a flask at prom, but that doesn’t stop her from trying to convince Valerie she deserves to attend anyway. Valerie doesn’t back down, and Sadie throws a hissy fit in response to not getting her way that includes screaming and aggressively throwing the contents of the breakfast buffet at no one in particular. These few moments are adequete proof that high school seniors are definitely not adults. 

3. T got a bench for the school on behalf of the class of 2015. Nice, right? The only problem is that she made a typo, resulting in a bench that reads: “Rest your weary bones here and reflect on the ass of 2015.” To be honest, though, giving future generations of high schoolers something to laugh at is arguably a better gift than giving them a heartfelt message to sit on.

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4. Matty doesn’t want to walk without Sadie, especially since the flask she was carrying was his — so Jenna tells her bud Valerie this in hopes that her high standing with the counselor will set both Matty and Sadie free. She is wrong. Valerie decides to ban both Matty and Sadie from walking, a decision that suggests that sometimes honesty maybe isn’t the best policy, after all. 

5. Theo and Cole strike early on during the graduation festivities when they hijack the sentimental slideshow of sweet photos to put on their own slideshow, one showcasing all the less-than-photogenic moments. Think T’s pink eye and Jenna’s body-cast era — not quite the kind of memories most people want to see blown up and shown in front of all their peers.

NEXT: Theo and Cole are throwing a secret kegger [pagebreak]

6. Graduation is going great — Matty gets to walk after Jenna gets the whole school to help defend him to Valerie; Sadie ends up giving a kickass (and completely Sadie) valedictorian speech despite Val’s protests — until Matty breaks the news to Jenna that, uh, they don’t have the whole summer together like they previously thought because, surprise, soccer camp at Berkeley starts that week. There was no great time for Matty to tell Jenna this, but hitting her with this at graduation’s happy, celebratory climax seems exceptionally misguided.

7. Theo and Cole are throwing a secret kegger at grad night, which Jake and T excitedly stumble upon. Jake pulls out some dollars to pay the two for some beer, but they don’t accept it — and they’re not being nice: The two tell Jake the beer’s on them because he’s peaked and everything is, as they say, going to be downhill for him post-high school. Are Theo and Cole ever likable? 

8. In an attempt to make Sadie happy, Lissa tricks Sergio into bringing his food truck to grad night, where she says Sadie will be ready to apologize to him. That doesn’t happen, and instead Sadie lets out her inner, as T would say, rude boy by Rihanna in Sergio’s direction. Lissa’s Parent Trap-inspired set-up seems like a failure until she eventually reveals her intentions to the two, who are making out against the food truck in no time. At least some people are having a good grad night.

9. Jake and T end up getting out all their frustration about Theo and Cole, about graduating, about change by throwing out a whole bunch of “meaningful” high school memories, an activity that ends in the two telling each other how happy they are to be spending this momentous night together. The once-couple almost kisses before they stop themselves and go in for a hug instead…but judging from the look on Jake’s face, he wasn’t completely on-board with the last-minute switch.

10. This isn’t an awkward moment, per se, but it needs to be said: Jenna and Matty’s tearful break-up conversation was full-on heartbreaking and perfectly captured the unexpected sadness of moving on from high school. Their split is only temporary because Jenna ends up seizing the moment, after getting some advice from Val, by accompanying Matty on his drive to Berkeley. As Jenna’s closing monologue indicates, though, their decision to take their relationship moment by moment and try out this whole distance thing won’t end well. But, hey: At least we — er, Jenna and Matty — will always have that blissful, post-graduation road trip.